Tag: M.W=200-300

These common heterocyclic compound, 213598-10-8, name is Methyl 3-bromo-4-isopropoxybenzoate, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. SDS of cas: 213598-10-8

Description 4: Methyl 3-cyano-4[(1-methylethyl)oxy]benzoate To a solution of methyl 3-bromo-4-[(1-methylethyl)oxy]benzoate (25 g, 91.575 mmol) (Description 3) in DMF (250 mL), under a nitrogen atmosphere, was added zinc cyanide (43 g, 366.3 mmol) and tetrakis(triphenylphosphine)palladium(0) (21 g, 18.32 mmol) and the reaction mixture heated to 120 C. and stirred overnight. After cooling, the mixture was filtered and the filtrate combined with an identical reaction performed on the same scale and DCM (1.5 L) and water (1.5 L) added. The organic phase was separated and the aqueous phase was extracted with DCM (3×300 mL). The combined organic layers were washed with water, dried over sodium sulfate and concentrated. The residue was purified by column chromatography on silica (petroleum ether :ethyl acetate (20:1) to afford the title compound (36 g). 1H NMR (CDCl3, 400 MHz) 5 ppm: 1.45 (6H, d, J=6.0 Hz), 3.92 (3H, s), 4.76 (1H, m), 7.00 (1H, d, J 9.0), 8.19 (1H, dd, J 9.0, 2.0 Hz), 8.26 (1H, d, J=2.0 Hz).

The synthetic route of Methyl 3-bromo-4-isopropoxybenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO WELLCOME HOUSE; US2012/283297; (2012); A1;,
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Adding a certain compound to certain chemical reactions, such as: 89901-03-1, name is Methyl 4′-bromo-[1,1′-biphenyl]-4-carboxylate, belongs to esters-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 89901-03-1, SDS of cas: 89901-03-1

To a round bottom flask was added methyl 4′-bromobiphenyl-4- carboxylate (2.0 g, 6.87 mmol, 1 .0 equiv) followed by a solution of racemic 2-trans- ethynylcyclopropyl)methanol (0.991 g, 10.30 mmol, 1.5 equiv) dissolved in THF (20 ml_). To this was added palladium dichloride bis-triphenylphosphine (241 mg, 0.343 mmol, 0.05 equiv), copper(l) iodide (131 mg, 0.687 mmol, 0.1 equiv), then triethylamine (6.87 ml_, 49.3 mmol, 7.18 equiv). The reaction was stirred at 75C for ~2 h. The reaction was cooled to room temperature, the solids filtered off, rinsing with THF. The solution was placed in the freezer for 5 days. Concentrate down to dryness. Add DCM and a precipitate forms. Filter precipitate, rinse with minimal DCM. TLC shows ppt contains mostly product (~1.5g solid). Triturate with 10%EtOAc in hexanes (5 mL), pipet off solvent, TLC shows solid contains product and liquid removed starting material-bromide and some baseline impurities. Additional 10%EtOAc in hexanes (5 mL) was added and stirred for 30 minutes, filtered, rinsed with 10%EtOAc in hexanes (5mL), and dried solid. Yielded 900 mg crude methyl 4′-(((1 ,2-irans)-2- (hydroxymethyl)cyclopropyl)ethynyl)biphenyl-4-carboxylate. 1 H NMR (DMSO-d6): delta 0.82-0.85 (m, 2H), 1.35-1.43 (m, 2H), 3.23-3.29 (m, 1 H), 3.40-3.42 (m, 1 H), 3.84 (s, 3H), 4.65-4.67 (t, 1 H), 7.43-7.45 (d, 2H), 7.67-7.70 (d, 2H), 7.80-7.82 (d, 2H), 7.99- 8.01 (d, 2H)

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, Methyl 4′-bromo-[1,1′-biphenyl]-4-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ACHAOGEN, INC.; KASAR, Ramesh; LINSELL, Martin Sheringham; AGGEN, James Bradley; LU, Qing (Jane); WANG, Dan; CHURCH, Tim; MOSER, Heinz E.; PATTEN, Phillip A.; WO2012/154204; (2012); A1;,
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Some common heterocyclic compound, 1214334-90-3, name is Methyl 2-bromo-4-(trifluoromethyl)benzoate, molecular formula is C9H6BrF3O2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. SDS of cas: 1214334-90-3

A 20 mL muwave vial was charged with methyl 2-bromo-4-(trifluoromethyl)benzoate (306 mg, 1.08 mmol), propane-2-sulfonamide (266 mg, 2.16 mmol), tris(dibenzylideneacetone)dipalladium (0)-chloroform adduct (112 mg, 0.108 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (188 mg, 0.324 mmol), potassium phosphate tribasic (1.15 g, 5.41 mmol) and toluene (10.0 mL). The vial was sealed, purged with nitrogen for 5 min, and then heated at 100 C. for 18 hours. The reaction was cooled to room temperature, concentrated and diluted with water. The mixture was extracted with EtOAc (3×), washed with brine, dried over MgSO4, filtered and concentrated. The crude product was purified by silica gel chromatography to afford methyl 2-((1-methylethyl)sulfonamido)-4-(trifluoromethyl)benzoate. LCMS-ESI+ (m/z): [M+H]+ calcd 326.07; found 326.00.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1214334-90-3, its application will become more common.

Reference:
Patent; Gilead Sciences, Inc.; Farand, Julie; Kaplan, Joshua A.; Notte, Gregory; Olen, Casey Lockwood; Sangi, Michael; Sperandio, David; (115 pag.)US2019/359565; (2019); A1;,
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Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 52787-14-1, name is Methyl 4-(2-methoxy-2-oxoethyl)benzoate, A new synthetic method of this compound is introduced below., HPLC of Formula: C11H12O4

Methyl 4-(2-methoxy-2-oxoethyl)benzoate (100 mg, 0.48 mmol), methanol (1.5 mL), water (1.5 mL) and anhydrous potassium carbonate (116 mg, 0.72 mmol) were added in a 10 mL single-neck flask, and the mixture was stirred at room temperature for 1.5 hours. After the materials had all reacted when being determined by TLC, solvent was removed in vacuo, and the residue was redissolved in ethyl acetate (1 mL) and separated by preparative thin layer chromatography (petroleum ether: ethyl acetate = 1:1) to give a product (white solid, 60 mg), with a yield of 64.4%. 1H NMR (400 MHz, CDCl3) delta 8.00 (d, J = 8.1 Hz, 2H), 7.35 (d, J = 8.0 Hz, 2H), 3.91 (s, 3H), 3.70 (s, 2H).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Fudan University; WANG, Yonghui; HUANG, Yafei; QIU, Ruomeng; TANG, Ting; (68 pag.)EP3581561; (2019); A1;,
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Electric Literature of 109232-37-3,Some common heterocyclic compound, 109232-37-3, name is Isobutyl 5-chloro-2,2-dimethylvalerate, molecular formula is C11H21ClO2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

General procedure: A solution of phenol (5 mmol) was added to a solution of sodium (114 mg, 5 mmol) in absolute EtOH (5 mL) at room temperature. After stirring for 30 min, a solution of suitable ethyl or isobutyl ester (5-bromovalerate, 5-bromo-2,2-dimethylpentanoic acid ethyl ester or 5-chloro-2,2-dimethylpentanoic acid isobutyl ester) (5 mmol) in absolute EtOH (5 mL) was added and the solution was stirred at reflux for 10-15 h. The solvent was removed under reduced pressure and the residue was dissolved into CH2Cl2 or ethyl acetate (25 mL) and washed with NaOH 2 N (3 × 25 mL). The organic layer was dried over Na2SO4 and concentrated under reduced pressure to yield the crude product that was purified by column chromatography to give the ester 9-14, 16 or 25-31. Ester 15 was obtained with the same procedure, but under milder conditions: K2CO3 (1.1 g, 8.38 mmol) was added to a solution of N-(4-hydroxyphenyl)-N’-phenylurea (531 mg, 2.33 mmol) in acetone (10 mL) at room temperature. After stirring for 30 min, a solution of ethyl 5-bromovalerate (488 mg, 2.33 mmol, 0.37 mL) in acetone (10 mL) was added. After 30 h the solvent was removed under reduced pressure and the residue was treated as above to give the compound 15.

The synthetic route of 109232-37-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; De Filippis, Barbara; Giancristofaro, Antonella; Ammazzalorso, Alessandra; D’Angelo, Alessandra; Fantacuzzi, Marialuigia; Giampietro, Letizia; MacCallini, Cristina; Petruzzelli, Michele; Amoroso, Rosa; European Journal of Medicinal Chemistry; vol. 46; 10; (2011); p. 5218 – 5224;,
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These common heterocyclic compound, 1000342-11-9, name is Methyl 3-amino-5-bromo-2-methylbenzoate, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Application In Synthesis of Methyl 3-amino-5-bromo-2-methylbenzoate

[01355] Step 4: Synthesis of cis and trans methyl 5-bromo-3-((4-((tert-butoxycarbonyl)amino) cyclohexyl) amino -2-methylbenzoate[01356] To a stirred solution of methyl 3-amino-5-bromo-2-methylbenzoate (5 g, 20.57 mmol) and tert-butyl (4-oxocyclohexyl)carbamate (5.6 g, 26.7 mmol) in methanol (50 mL), acetic acid ( 1 .2 g, 20.57 mmol) was added and reaction stirred at room temperature for 8 h. Then sodium cyanoborohydride (1.6 g, 26.74 mmol) was added at OoC and reaction stirred overnight. On completion, solvent was removed under reduced pressure and crude material was purified by column chromatography twice eluting with ethyl acetate: hexane to afford (4g , 44%) of less polar cis isomer and (3g, 33%) of the pure more polar trans isomer.

The synthetic route of Methyl 3-amino-5-bromo-2-methylbenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; EPIZYME, INC.; EISAI CO., LTD.; KUNTZ, Kevin, Wayne; CHESWORTH, Richard; DUNCAN, Kenneth, William; KEILHACK, Heike; WARHOLIC, Natalie; KLAUS, Christine; ZHENG, Wanjun; WO2012/142513; (2012); A1;,
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Synthetic Route of 99548-55-7, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 99548-55-7, name is Methyl 4-bromo-2-methylbenzoate, This compound has unique chemical properties. The synthetic route is as follows.

Example 33B Methyl 4-bromo-2-(bromomethyl)benzoate A solution of Example 33A (1.02 g, 4.47 mmol) in CCl4 (22 mL) was treated with AIBN (0.065 g, 0.4 mmol) and NBS (0.955 g, 5.4 mmol), heated to reflux for 4 hours, washed with water, dried (Na2SO4), filtered, and concentrated to provide the desired product (1.1 g, 79%).

The chemical industry reduces the impact on the environment during synthesis Methyl 4-bromo-2-methylbenzoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Li, Qun; Woods, Keith W.; Zhu, Gui-Dong; Fischer, John P.; Gong, Jianchun; Li, Tongmei; Gandhi, Virajkumar; Thomas, Sheela A.; Packard, Garrick K.; Song, Xiaohong; Abrams, Jason N.; Diebold, Robert; Dinges, Jurgen; Hutchins, Charles; Stoll, Vincent S.; Rosenberg, Saul H.; Giranda, Vincent L.; US2003/187026; (2003); A1;,
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In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 41841-16-1, name is Methyl 2-(4-bromophenyl)acetate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C9H9BrO2

To a stirred solution of 100 g methyl-(4-bromophenyl)acetate(9, 0.436 mol) in 300 cm3 tetrahydrofuran, 95 g sodium methoxide (1.75 mol) was added at 0-5 C and maintained for 1 h. 80 g dimethyl carbonate (0.88 mol)was added at 0-5 C over a period of 2 h. The reaction mass was maintained at 25-30 C until the completion ofthe reaction (monitored by HPLC). After completion of the reaction, tetrahydrofuran was concentrated under reduced pressure at 45 C to obtain the syrup. The syrup was diluted in 500 cm3 water and the product was extracted in250 cm3 dichloromethane. The organic layer was concentrated under reduced pressure at 45 C to obtain the thick solution which was dissolved in 200 cm3 isopropyl alcoholat 70 C and maintained for 1 h. The solution was cooled to 0 C and maintained for 60 min. The obtained solid was filtered, washed with isopropyl alcohol, and dried at 50-55 C for 4-6 h to provide 10. Yield: 80 g; purity by HPLC: 99%; m.p.: 72-76 C. The spectral data of compound 10 were found to agree with the reported data [8].

The synthetic route of 41841-16-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Jagtap, Kunal M.; Niphade, Navnath C.; Gaikwad, Chandrashekhar T.; Shinde, Gorakshanath B.; Toche, Raghunath B.; Joshi, Divyesh R.; Mathad, Vijayavitthal T.; Monatshefte fur Chemie; vol. 149; 3; (2018); p. 653 – 661;,
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Ester – an overview | ScienceDirect Topics

Reference of 54535-22-7, A common heterocyclic compound, 54535-22-7, name is Diethyl 2-((phenylamino)methylene)malonate, molecular formula is C14H17NO4, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

j00330J A 1 L three-necked flask fitted with a mechanical stirrer was charged with 2- phenylaminomethylene-malonic acid diethyl ester (26.3 g, 0.100 mol), polyphosphoric acid (270 g) and phosphoryl chloride (750 g). The mixture was heated to 70 C and stirred for 4 h. The mixture was cooled to room temperature and filtered. The residue was treated with aqueous Na2CO3 solution, filtered, washed with water and dried. 4- Hydroxyquinoline-3-carboxylic acid ethyl ester was obtained as a pale brown solid (15.2 g, 70%). The crude product was used in next step without further purification.

The synthetic route of 54535-22-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; CHU, Cathy; DOKOU, Eleni; HASELTINE, Eric L.; MOSKOWITZ, Samuel; OVERHOFF, Kirk A.; ROBERTSON, Sarah; WALTZ, David; (204 pag.)WO2019/10092; (2019); A1;,
Ester – Wikipedia,
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In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 90971-88-3, name is Methyl 2-bromo-5-methylbenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Safety of Methyl 2-bromo-5-methylbenzoate

Example 15; Synthesis of 5-methyl-2-triisopropylsilanylsulfanyl-benzoic acid methyl ester (Method 15.) 2-Bromo-5-methyl-benzoic acid methyl ester (2.06 g, 9.00 mmol), tris(dibenzylideneacetone)dipalladium (0) (83 mg, 0.09 mmol), bis(2-diphenylphosphinophenyl)ether (97 mg, 0.18 mmol), sodium tert-butoxide (1.00 g, 10.4 mmol), triisopropylsilanethiol (1.37g, 7.2 mmol) and dry toluene (10 mL) are all placed in an Emrys Optimizer EXP 20 mL microwave reactor tube. The reaction vessel is sealed and subjected to microwave heating at 150 C. for 30 minutes. Upon cooling the mixture is poured onto a plug of silica and the product is eluted with ethyl acetate-heptane (2:8). This furnishes the title compound as an oil, which is used in the next step without further purification.

The synthetic route of 90971-88-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kehler, Jan; Juhl, Karsten; Norgaard, Morten Bang; US2006/287386; (2006); A1;,
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Ester – an overview | ScienceDirect Topics